JP2016502544A5 - - Google Patents
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- JP2016502544A5 JP2016502544A5 JP2015545510A JP2015545510A JP2016502544A5 JP 2016502544 A5 JP2016502544 A5 JP 2016502544A5 JP 2015545510 A JP2015545510 A JP 2015545510A JP 2015545510 A JP2015545510 A JP 2015545510A JP 2016502544 A5 JP2016502544 A5 JP 2016502544A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- independently
- arylalkyl
- alkyl
- heteroarylalkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 238000000034 method Methods 0.000 claims description 216
- 125000000217 alkyl group Chemical group 0.000 claims description 165
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 145
- 201000011510 cancer Diseases 0.000 claims description 122
- 206010028980 Neoplasm Diseases 0.000 claims description 120
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 120
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 101
- 125000003118 aryl group Chemical group 0.000 claims description 98
- 125000001072 heteroaryl group Chemical group 0.000 claims description 98
- 125000003545 alkoxy group Chemical group 0.000 claims description 97
- 125000000623 heterocyclic group Chemical group 0.000 claims description 92
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 88
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 88
- 125000004104 aryloxy group Chemical group 0.000 claims description 88
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 88
- 125000005326 heteroaryloxy alkyl group Chemical group 0.000 claims description 88
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 88
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 84
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 82
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 76
- 125000004945 acylaminoalkyl group Chemical group 0.000 claims description 72
- 125000003342 alkenyl group Chemical group 0.000 claims description 72
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 56
- 206010006187 Breast cancer Diseases 0.000 claims description 55
- 208000026310 Breast neoplasm Diseases 0.000 claims description 55
- 210000004027 cell Anatomy 0.000 claims description 51
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 49
- 210000003719 b-lymphocyte Anatomy 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 33
- 230000036210 malignancy Effects 0.000 claims description 29
- 125000004442 acylamino group Chemical group 0.000 claims description 24
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 24
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 24
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 24
- -1 rather than the H Chemical compound 0.000 claims description 24
- 238000011282 treatment Methods 0.000 claims description 23
- 239000002246 antineoplastic agent Substances 0.000 claims description 20
- 229940127089 cytotoxic agent Drugs 0.000 claims description 20
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 19
- 208000001976 Endocrine Gland Neoplasms Diseases 0.000 claims description 18
- 208000029559 malignant endocrine neoplasm Diseases 0.000 claims description 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 125000002252 acyl group Chemical group 0.000 claims description 16
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 16
- 125000002837 carbocyclic group Chemical group 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 206010009944 Colon cancer Diseases 0.000 claims description 13
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 13
- 208000008839 Kidney Neoplasms Diseases 0.000 claims description 13
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 13
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- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 8
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- 229960002438 carfilzomib Drugs 0.000 claims description 6
- BLMPQMFVWMYDKT-NZTKNTHTSA-N carfilzomib Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC(C)C)C(=O)[C@]1(C)OC1)NC(=O)CN1CCOCC1)CC1=CC=CC=C1 BLMPQMFVWMYDKT-NZTKNTHTSA-N 0.000 claims description 6
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- UVSMNLNDYGZFPF-UHFFFAOYSA-N pomalidomide Chemical compound O=C1C=2C(N)=CC=CC=2C(=O)N1C1CCC(=O)NC1=O UVSMNLNDYGZFPF-UHFFFAOYSA-N 0.000 claims description 6
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- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims description 5
- IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 claims description 4
- UEJJHQNACJXSKW-UHFFFAOYSA-N 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1CCC(=O)NC1=O UEJJHQNACJXSKW-UHFFFAOYSA-N 0.000 claims description 4
- AOJJSUZBOXZQNB-VTZDEGQISA-N 4'-epidoxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-VTZDEGQISA-N 0.000 claims description 4
- STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 claims description 4
- GAGWJHPBXLXJQN-UORFTKCHSA-N Capecitabine Chemical compound C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1[C@H]1[C@H](O)[C@H](O)[C@@H](C)O1 GAGWJHPBXLXJQN-UORFTKCHSA-N 0.000 claims description 4
- GAGWJHPBXLXJQN-UHFFFAOYSA-N Capecitabine Natural products C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1C1C(O)C(O)C(C)O1 GAGWJHPBXLXJQN-UHFFFAOYSA-N 0.000 claims description 4
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims description 4
- HTIJFSOGRVMCQR-UHFFFAOYSA-N Epirubicin Natural products COc1cccc2C(=O)c3c(O)c4CC(O)(CC(OC5CC(N)C(=O)C(C)O5)c4c(O)c3C(=O)c12)C(=O)CO HTIJFSOGRVMCQR-UHFFFAOYSA-N 0.000 claims description 4
- 102000009127 Glutaminase Human genes 0.000 claims description 4
- 108010073324 Glutaminase Proteins 0.000 claims description 4
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 claims description 4
- NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 claims description 4
- RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 claims description 4
- VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 claims description 4
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- STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 claims description 4
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| US8604016B2 (en) | 2011-11-21 | 2013-12-10 | Calithera Biosciences Inc. | Heterocyclic inhibitors of glutaminase |
| JP6275153B2 (ja) | 2012-11-16 | 2018-02-07 | キャリセラ バイオサイエンシーズ， インコーポレイテッド | ヘテロ環式グルタミナーゼ阻害剤 |
| EP3092235A2 (en) | 2014-01-06 | 2016-11-16 | Rhizen Pharmaceuticals S.A. | Novel inhibitors of glutaminase |
| WO2015138902A1 (en) * | 2014-03-14 | 2015-09-17 | Calithera Biosciences, Inc. | Combination therapy with glutaminase inhibitors |
| MX2016014143A (es) | 2014-04-30 | 2017-02-15 | Pfizer | Derivados de diheterociclo enlazado a cicloalquilo. |
| GB201409624D0 (en) | 2014-05-30 | 2014-07-16 | Astrazeneca Ab | 1,3,4-thiadiazole compounds and their use in treating cancer |
| AU2015274361B2 (en) * | 2014-06-13 | 2020-11-05 | Calithera Biosciences, Inc. | Combination therapy with glutaminase inhibitors |
| CN107074805B (zh) | 2014-07-03 | 2021-02-26 | 德州大学系统董事会 | 用于治疗疾病的gls1抑制剂 |
| WO2016004417A1 (en) * | 2014-07-03 | 2016-01-07 | Board Of Regents, University Of Texas System | Gls1 inhibitors for treating disease |
| WO2016007647A1 (en) * | 2014-07-09 | 2016-01-14 | The Johns Hopkins University | Glutaminase inhibitor discovery and nanoparticle-enhanced delivery for cancer therapy |
| WO2016014890A1 (en) * | 2014-07-24 | 2016-01-28 | Calithera Biosciences, Inc. | Treatment of multiple myeloma with heterocyclic inhibitors of glutaminase |
| EA037738B1 (ru) * | 2014-08-07 | 2021-05-17 | Калитера Байосайенсиз, Инк. | Кристаллические формы ингибиторов глутаминазы |
| WO2016054388A1 (en) * | 2014-10-03 | 2016-04-07 | University Of Pittsburgh - Of The Commonwealth System Of Higher Education | Glutaminase inhibitors |
| JP6768693B2 (ja) * | 2015-03-30 | 2020-10-14 | キャリセラ バイオサイエンシーズ， インコーポレイテッド | グルタミナーゼ阻害剤を投与する方法 |
| US10441587B2 (en) * | 2015-04-06 | 2019-10-15 | Calithera Biosciences, Inc. | Treatment of lung cancer with inhibitors of glutaminase |
| EP3316887B1 (en) | 2015-06-30 | 2020-04-08 | Board of Regents, The University of Texas System | Gls1 inhibitors for treating disease |
| WO2017062354A1 (en) * | 2015-10-05 | 2017-04-13 | Calithera Biosciences, Inc. | Combination therapy with glutaminase inhibitors and immuno-oncology agents |
| CN109503570B (zh) * | 2015-12-18 | 2020-08-25 | 诺言医药科技(上海)有限公司 | 一种含有索拉非尼的药物组合物及其应用 |
| US10150753B2 (en) * | 2015-12-22 | 2018-12-11 | Board Of Regents, The University Of Texas System | Salt forms and polymorphs of (R)-1-(4-(6-(2-(4-(3,3-difluorocyclobutoxy)-6-methylpyrdin-2-yl)acetamido) pyridazin-3-yl)-2-fluorobutyl)-N-methyl-1H-1,2,3-triazole-4-carboxamide |
| KR102456433B1 (ko) | 2016-03-02 | 2022-10-19 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 에리불린-기반 항체-약물 콘주게이트 및 사용 방법 |
| CN107474024B (zh) * | 2016-06-08 | 2022-12-13 | 北京赛林泰医药技术有限公司 | 一种谷氨酰酶抑制剂及其组合物和用途 |
| WO2018039544A1 (en) | 2016-08-25 | 2018-03-01 | Calithera Biosciences, Inc. | Combination therapy with glutaminase inhibitors |
| CN109982703A (zh) * | 2016-08-25 | 2019-07-05 | 卡利泰拉生物科技公司 | 用谷氨酰胺酶抑制剂的组合疗法 |
| US20180055825A1 (en) * | 2016-08-25 | 2018-03-01 | Yu Liang | Treatment of cancer with inhibitors of glutaminase |
| US10086987B2 (en) * | 2016-10-13 | 2018-10-02 | Altria Client Services Llc | Reseal label for box in a box re-sealable pack |
| CN107137401A (zh) * | 2017-03-28 | 2017-09-08 | 刘纪君 | 一种治疗产后抑郁症的药物组合物 |
| CN106860460B (zh) * | 2017-03-29 | 2019-04-23 | 上海市第一人民医院 | 谷氨酰胺酶抑制剂cb-839在制备治疗雌激素敏感型子宫内膜癌的药物中的应用 |
| JP7361687B2 (ja) | 2017-10-18 | 2023-10-16 | ボード オブ レジェンツ，ザ ユニバーシティ オブ テキサス システム | グルタミナーゼ阻害薬療法 |
| CN110746416A (zh) * | 2019-09-05 | 2020-02-04 | 中国药科大学 | 含有三氮唑结构的谷氨酰胺酶gls1抑制剂或其可药用的盐、其制备方法及用途 |
| CN111514460B (zh) * | 2020-05-22 | 2021-12-14 | 西安交通大学 | 大气压冷等离子体在抑制谷氨酰胺酶活性方面的用途及酶抑制剂 |
| KR20230001587A (ko) * | 2021-06-28 | 2023-01-05 | 연세대학교 산학협력단 | 암의 예방 또는 치료용 약학 조성물 |
| CN114805346A (zh) * | 2021-07-08 | 2022-07-29 | 成都硕德药业有限公司 | 杂环类衍生物、其制备方法及用途 |
| KR102649592B1 (ko) * | 2021-08-18 | 2024-03-20 | 한국화학연구원 | 신규한 마크로사이클 화합물, 이의 제조방법, 이를 유효성분으로 포함하는 암 또는 자가면역질환의 예방 또는 치료용 약학적 조성물 |
| CN116023375A (zh) * | 2021-10-25 | 2023-04-28 | 成都苑东生物制药股份有限公司 | 一种杂环类衍生物、其制备方法及用途 |
| CN114057601B (zh) * | 2021-12-14 | 2024-11-08 | 重庆腾泽化学有限公司 | 一种丁二酸二酰肼的制备方法 |
| CN114805334B (zh) * | 2022-05-24 | 2023-06-09 | 深圳大学 | 一种QC和GSK-3β多靶向抑制剂及其制备方法与应用 |
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| US6451828B1 (en) * | 2000-08-10 | 2002-09-17 | Elan Pharmaceuticals, Inc. | Selective inhibition of glutaminase by bis-thiadiazoles |
| WO2005113798A2 (en) * | 2004-04-15 | 2005-12-01 | University Of Florida Research Foundation, Inc. | Proteolytic markers as diagnostic biomarkers for cancer, organ injury and muscle rehabilitation/exercise overtraining |
| TWI478709B (zh) * | 2008-02-19 | 2015-04-01 | Earnest Medicine Co Ltd | A useful oral or enteral composition for the recovery of bodily functions |
| WO2011143160A2 (en) * | 2010-05-10 | 2011-11-17 | The Johns Hopkins University | Metabolic inhibitor against tumors having an idh mutation |
| WO2012006506A1 (en) * | 2010-07-09 | 2012-01-12 | Massachusetts Institute Of Technology | Metabolic gene, enzyme, and flux targets for cancer therapy |
| RS59705B1 (sr) * | 2011-11-21 | 2020-01-31 | Calithera Biosciences Inc | Heterociklični inhibitori glutaminaze |
| JP6275153B2 (ja) * | 2012-11-16 | 2018-02-07 | キャリセラ バイオサイエンシーズ， インコーポレイテッド | ヘテロ環式グルタミナーゼ阻害剤 |
| WO2014079011A1 (en) * | 2012-11-22 | 2014-05-30 | Agios Pharmaceuticals, Inc. | Heterocyclic compounds for inhibiting glutaminase and their methods of use |
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